D'ANNA, Francesca

MARULLO, Salvatore

NOTO, Renato

RIZZO, Carla

VITALE, Paola

Archivio istituzionale della ricerca - Università di Palermo

2.Socieid Chimico ltqliono,.i{*l;,,tl.;?.;;;:.1_.F'#,*."Ti<t,'ALMA MATER STUDIORUMUNIVERSITA DI BOLOGNAXXXVI Convegno Nazionale dellaDivisione di Chimica OrganicaSocieti Chimica ltalianaAtti del ConvegnoBOLOGNA L3-I7 settembre 2015Alma Mater Studiorum - Universi t i  d i  BolognaAule Complesso Belmeloro, via Belmeloro t4, BolognaPC48Task-specific dicationic ionic liquids used as reaction media forMichael addition.Carla Rizzol, Francesca D'Annal, Salvatore Marullol, Paola Vitalel, Renato NotortDipartimento STEBICEF, Sezione di Chimica, Viale delle Scienze-Parco d'Orleans II, 90128 Palermo,halY'e -m a i I : fu ancesca.danna@uniPa.itNowadays one of the main goals in organic chemistry is the research ofincreasing efficiency in chemical processes taking care of the environmental impact.In this context the choice of the right catalysts and solvents for organic reactionsbecomes crucial. For this reason in the last decades, ionic liquids have been appliedas altemative solvents thanks to their low flammability, vapor pressure and highstructural organization.l If a catalyst is tethered in the cation or in the anion of theionic liquids, they are called "task-specific ionic liquids". The ensemble of catalystand solvent in one compound increases the kinetic mobility and allows a largeoperational surface area.zwe have recently studied the properties and the catalytic ability of noveldiimidazolium ionic liquids bearing an imidazole as basic functionality.' Propertiesofthese ionic liquids, such as thermal stability, catalytic ability and recyclability arestrongly dependent on the nature ofthe anion used.With this in mind, we are now interested in the study of Michael addition ofmalonitrile to trans-calchone (Scheme l), a base catalyzed reaction that leads to akey precursor for the synthesis of some biological and pharmaceutical products. Inaddition to the basic functionality present on the cationic unit, chiral anions such asrartrate, proline, phenilalanine, (R)-(-)-1,1'binaphtyl-2,2'diyl-phosphate, have beenused in order to analyze stereochemical aspects ofthe reaction, studying their effectson reaction time, percentage yields and enantiomeric excess., l  l^^i '  I  @[ -J a:.;vz' ] Ir  t t'15r-c"r '  l  I i iJI({*,,*t,LReaction media for Michael addil ionO lonic liquids@ Basic functionalityO chiral an:ons? * dt'1j  . l  ' - '  I  .J  . .nN.8 r  I  ' . l  .Scheme 1 Task-specific ionic liquids used for the study of Michael additionReferences:1. Dupont, I.; Acc. Chem. Res. 2011, 44, 1223.2. a)Lee,S.-G.; Chem. Commun. 2006,1049. b) Sawant, A. D.; Raut, D. G.; Darvatkar, N' B';Salunkhe, M. M; Green Chem. Lett. Rev " 2011, 4, 41.3. a) D'Anna, F.; Gunaratne' N.H. Q.;Lazzara, G.; Noto, R.; Rizzo, C'; Seddon, K'P.'; Org' Biomol'Chim. 2013, I I , 5836. b) Rizzo, C.; D'Anna, F.; Marullo, S.; Noto, k; J. Org Chem 2014, 79' 8678't tJ

Task-specific dicationic ionic liquids used as reaction media for Michael addition

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Task-specific dicationic ionic liquids used as reaction media for Michael addition

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Archivio istituzionale della ricerca - Università di Palermo